Scout Cambridge: A Stitch in Time

Gary Drinkwater got his start in 1978 at the world-famous Louis Boston, a menswear institution that recently closed after 85 years. He interviewed for a visual merchandising position, but when that had already been filled, he moved over to sales. It was there that he learned how to be not just a salesman but a consultant. He quickly realized it wasn’t necessarily clothing people wanted, but an experience.

“It’s a relationship business,” he says now, reflecting on those early days. “And relationships turn into long-lasting ones. Some of the first guys I waited on in 1978 are still shopping with me today.”

Drinkwater is impeccably dressed, with posture that would put a Catholic school nun to shame. He has a thoughtful, measured way of speaking, and he takes time to pause before he answers a question.

This is all to say: Gary Drinkwater is the man you trust to help make you look good.

When you walk out of Drinkwater’s—which opened outside of Porter Square in 2004—you’re leaving with more than just a fine piece of clothing. At his award-winning shop, Drinkwater doesn’t carry any big brand names—if you can find it in a department store, you won’t find it here. He doesn’t stock anything you can buy online, either. And if you’ve heard of the store at all, it was almost assuredly from a friend or well-dressed stranger. “We haven’t spent one dime on advertising since the day we opened,” Drinkwater says proudly.

The clientele of Drinkwater’s isn’t just well-to-do older gentlemen. The much-maligned millennial now makes up a significant portion of the customer base. “The millennial,” Drinkwater says, no hint of malice in the word, “has made a decision that he doesn’t want to look like the guys that preceded him. He wants to be a little smarter about the way he dresses. He’s very interested in fabric and construction and all the various elements that put a wardrobe together.”

Keeping an eye on these nearly imperceptible trends allows Drinkwater to remain on top. He owns the store with his wife, Teresa Borges. (They met as coworkers at Louis.) Together, they travel to trade shows and meet with suppliers to ensure their store remains the place to go when you need to make an impression or update your closet. Drinkwater wants his customers to have a memorable experience every time they’re in the shop, and he wants them to leave the store looking really, really good.

Because, more than the beautiful jackets, custom-made shirts and fine shoes, it’s the people Drinkwater loves. “I’m a people person. I just love it,” he says. “I think it’s one of the reasons I’ve stayed. I’ve been able to meet the most incredible people in the world. That’s the fun part of my business.”

What keeps him coming back day in and day out—sometimes for 12 hours a day? He pauses for a moment in his thoughtful way, then quips, with a hearty laugh, “What else am I going to do?”

This story originally appeared in the January/February issue of Scout Cambridge.